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Synfacts 2010(8): 0857-0857  
DOI: 10.1055/s-0030-1257743
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Oseltamivir

Contributor(s): Philip Kocienski
J. Weng, Y.-B. Li, R.-B. Wang, F.-Q. Li, C. Liu, A. S. C. Chan, G. Lu*
Sun Yat-sen University, Guangzhou and The Hong Kong Polytechnic University, P. R. of China
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

An eleven-step, azide-free synthesis of oseltamivir (21% overall yield) began with cheap diethyl d-tartrate. The key steps were (1) an aza-Henry reaction (C → D), whose stereochemistry is controlled by a tert-butanesulfinimine chiral auxiliary, and (2) a tandem nitro-Michael addition-HWE reaction to create the carbocycle H.